should you date a coworker?

byAlison GreenonOctober 18, 2012

A reader writes:

I work in a small office, and I’ve recently become close with one of my coworkers. There’s been some flirting, and I think she’d say yes if I asked her out. Some of my friends who have dated at work are warning me not to mix business and pleasure, but I figure we’re both grown-ups. Is there any real reason not to give it a shot, as far as potential impact on my career or professional standing?

To read my answer to this question, visit the Intuit QuickBase blog … where I list the five biggest downsides to dating a coworker that people often don’t think about when they’re in the grip of a new romance.

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{80 comments… read them below }

My personal feeling is NOOOOOO! On the other hand, I do know couples where this worked out okay, but in all instances they were working in different departments in different parts of the building under different managers doing different functions.

I think there’s a difference between “people who work for the same company” and “coworkers,” especially at a big company. I would have a much easier time dating a man who worked in the accounting department on the fifth floor if I worked in marketing on the 12th than I would dating another member of the marketing department. It sounds like the OP’s thinking about asking out someone he works directly with every day, although I guess it’s not 100% clear.

+1 I was planning to say something like this. It really depends of how closely you work together. The more often you interact and see each other every day, the worse an idea it is to start dating.

Frankly the LW’s situation seems like a bad one for a dating a co-worker because of the small office decription. He or she should be very serious about the relationship before taking the risks to date a co-worker in a small office setting.

Yeah, the smallness of the office seems like a huge problem. I’d be hesitant to be close friends with a co-worker in a small office. Every interpersonal thing is magnified when there are only a few other people.

I met my ex-boyfriend at work and we worked for the same company for the first 1.5 years of our 4 year relationship. The *only* reason I even considered going out with him on our first date was because he worked in the warehouse, while I worked upstairs in the front offices. We had to go out of our way to see each other during the work day. In the early days I was very reassured by the fact that even if it didn’t work out, I could probably count on one hand the number of times I could expect to see him in any given year.

This fact also played to my advantage during another potentially fraught situation that Alison didn’t address — what happens if your coworker/romantic partner is fired or leaves on bad terms?

Our company wasn’t large, probably about 150-200 workers, but Warehouse people and Upstairs people barely knew each other. It was like we lived in separate countries and spoke different languages. When some poor management practices plus my ex’s personality clashed spectacularly and he quit before he could be fired, the people that I worked with day to day knew nothing about that situation, so I didn’t need to deal with that weirdness at all in public. My loyalties were not tested, I wasn’t expected to defend/explain my ex’s situation, no conversations were quickly hushed up when I walked into the room, etc. It took most of my coworkers a few months to realize that he no longer even worked there.

Some of the upper management who knew about our relationship (it was never secret but we never made a general announcement about it either) might have looked at me with some skepticism, but I was able to keep my head down, do my job, and not insert myself in another department’s drama. There was never any blowback on me. In fact a friendship that I had with a coworker several years later at that same company probably caused me more problems professionally than my ex’s dramatic exit.

I can almost guarantee that will not be the situation in such a small office setting.

I avoided this throughout my career for some of the reasons Alison mentioned until last fall when a friendship with a coworker unexpectedly grew into something more. Because I worried about us becoming the center of office gossip (we worked at a small-ish nonprofit) or people doubting if we could still work together professionally, we kept our relationship under wraps for 8 months. At that time I got a new job (for several reasons other than being tired of hiding our relationship at work).

We are now engaged and everyone at my previous (and fiance’s current) workplace knows and is very supportive of our relationship. His boss even mentioned to me that it wouldn’t have been a problem if I had stayed at the organization and we had continued our relationship in the open, since we were not in a supervisor/employee situation.

That being said, I agree there are many potential pitfalls. Definitely don’t do it if you don’t see the relationship leading somewhere serious. There are too many risks if you just want a fling. Also be aware that depending on how the relationship develops, one of you may need to find a new job.

I married a guy I met at work. It was my first “real” job in my field out of college and we became fast friends and eventually, it was impossible for us to not date. At that point I was already looking for another job.

Like you we kept it under wraps and most people didn’t even find out until after I had found a new job and left the company. When we got married, all of his coworkers (it was a fairly small place and they all knew me, too) went in on a nice gift for us.

So yeah, it can work out. I still don’t recommend using the office as a dating pool, though, because I know my situation is the exception and not the rule.

I met my husband at work. It was a couple weeks after my HS graduation and a summer job for me, but he worked there full time. Originally, I was not planning to continue the job OR the relationship past August : ) We have been married a decade and a half.

I have always thought it would have been more awkward at a “real” job, but I know several pairs of coworkers who met, dated, and married each other, and a few who dated and it didn’t work out. It seems to be fine in our company culture.

I know couples who have met at work, but I also know office romances that have imploded spectacularly. (“We’re both grown-ups” can fall by the wayside VERY quickly when a relationship ends, no matter how the couple met.) In general I avoid dating people I meet at work. I haven’t yet met a guy at work that’s worth the potential fallout; I suppose if I do, I’ll cross that bridge when I get to it. (I’ve also historically worked in offices with more women than men, so as a straight woman, that limits my dating options.)

If you’re really interested, certainly no one can stop you – but I’d echo Samantha and say don’t ask out your coworker unless you see it being serious. If you just want something casual and fun, put up an OKCupid profile. And you call yourselves coworkers so I assume she doesn’t report to you – if there’s any sort of power imbalance, I really don’t think you should ask her out.

Or any potential for a power imbalance. It’s like Alison said, you may be cut out of the running for promotions or good projects because your boss will think you can’t be impartial. And if you both decide to keep your relationship a secret at the office, you better make damn sure you’re good at doing that.

Meh… like I said below, I had a few “casual” work romances. although honestly all of them were at temp gigs when I was in college and I didn’t even live full time in the city, so maybe that changed things and made it easier to not get the uncomfortables.

But I think your point is basically sound and that IN GENERAL it’s a bad idea to treat the office like a speed dating event.

I like this comment, because it touches on the bottom line in dating coworkers. Dating a coworker is just like dating any other person, in that it might work out or might not. It’s not doomed to fail, and I don’t think anyone’s really saying that when they say “Don’t date a coworker!” But if it does fail, and plenty of relationships do for all sorts of unpredictable reasons, the potential fallout is so much worse because you can’t really sever a professional relationship just because you’ve ended a personal one.

It’s really just another facet of the dilemma of mixing your work life and personal life. It seems sometimes like the only place you meet people as an adult is at work, so it can feel like an obvious place to make friends. But mixing the personal and professional is always fraught with potential complications so it has to be treated with more care, or avoided entirely.

Something like this happened to me recently. I was friends with somebody for awhile before I started working with them, and eventually I developed feelings for her and wanted to ask her out.

My suggestion (and what I did,) be it awkward, is to ask your boss what the company’s policy is concerning dating coworkers. In my case, talking to him was a relief, as not only did he say it was ok so long as it doesn’t interfere with our professional relationship, but in that he said that he trusted me because he knew me to be a professional, mature adult. You have to look at yourself and ask yourself if you have the maturity to handle a relationship, a rejection, or even a future break up. Also, look at the other person too. Do you think the other person will be able to maintain a professional demeanor around you, whether that person returns or rejects your advances?

As for me, I wound up getting turned down, but that has not affected our friendship or our work relationship because we are both mature, adults.

“Also, look at the other person too. Do you think the other person will be able to maintain a professional demeanor around you, whether that person returns or rejects your advances?”

I agree with this. OP, you may be looking at Alison’s list and think that you can handle all of it but what about the other person? What about any of their friends in the office that might give you the stink-eye if you broke up? Or what if everything worked out beautifully and after you got married and had a couple of kids, the business folded and you both were out of a job at the same time?

I completely understand this is a hard decision. The last think you want is to think “what if” for the rest of your life. But as my mom used to say: if it’s meant to be, it will still be there for you later. She meant don’t marry the high school boy because you’re afraid he won’t wait for you until you’ve graduated college. But I think it might work out in this instance for you, too. Is there any reason to rush?

You have to look at yourself and ask yourself if you have the maturity to handle a relationship, a rejection, or even a future break up. Also, look at the other person too. Do you think the other person will be able to maintain a professional demeanor around you, whether that person returns or rejects your advances?

So very true! I have a good friend who started dating a coworker (same department) after working together for years. Technically, they weren’t supposed to be dating, but they were the kind of people that actually kept it a secret for several years! Eventualyl they moved in together and he transferred to another location and they are still going strong. Probably two fo the most mature people I’ve ever met.

On the other hand, I worked with a friend who dated a coworker from another location, who sometimes worked at our location. It turned out badly and it eventually was completely awkward and miserable for me to even work with him. He did not handle it well.

This decision takes some serious soul searching, and my observations have lead me to believe that you probably will want to already know this person very well.

So I have gone on dates with coworkers. None ended particularly badly, but likely because I didn’t mess around with people I actually work with day-to-day. I dated guys who worked in different departments/floors/cities and so I could easily put them out of mind once things didn’t work out.

I have seen office romances work and FAIL EPICALLY. When they work it seems to be because the couple keeps the office blissfully unaware until things are very serious. When they fail it’s been because they work alongside each other every single day and can’t sit in the same room together hating each other without making everyone uncomfortable.

An old friend of mine dated the awfullest guy in our office and just KEPT GETTING BACK TOGETHER because they worked like 15 feet from each other. Ugh. He was the worst. It went on FOR YEARS.

I liked Alison’s articles, but I am one that says it depends. I dated a co-worker ( more than one when I was younger) and I ended up marrying the guy. We dated three months and became engaged and have been married over 30 years. I was just a secretary and he rose on up in the company. Sometimes, it can be the best match.

I dated a guy I worked with on and off for about 2 years in my early 20’s. We worked on the same floor but different divisions of the same dept. We kept it a secret from our co-workers at his request. While we were seeing each other, I knew he had a good female friend of several years who worked on another floor. I always suspected that he wanted more than a friendship from her, but I said anything about it. Then, while we were broken up, he dated her for awhile and was bragging about it to co-workers. This was incredibly hurtful to me, because I felt like I was an embarrassing secret to him while she was someone he was excited about.

Oof, yeah, that should always be a red flag. I promptly dumped the one guy who dared to ask me to keep our relationship a secret. There’s no good reason for that, even with co-workers. It doesn’t even matter whether he’s “embarrassed” or keeping multiple girlfriends/wives – he’s disrespectful and not worth wasting a moment of your time on at that point.

There’s a huge difference between keeping a relationship at work low-key and keeping it a secret. It’s one thing if casual observers never realize you’re dating. It’s another thing if a co-worker asks about your significant other and you end up having to lie about it.

It’s been many years since we stopped seeing each other so I’m well over it now, and I didn’t mean to be a big bring-down by sharing my experience. Just wanted to point out sometimes people hurt you, and it’s just that much harder to get over when you have to see them every day.

Eh. I can understand keeping it under wraps at work. That’s what my now-husband and I did. We never really lied about it because no one really asked. We were just that casual about it at the office. People knew we were friends and maybe some suspected we were seeing each other casually. No one expected us to get married or realized we were actually serious about each other.

Sometimes it’s just easier to not have everyone up in your personal life when you’re at work. It’s not about anyone being embarrassed about the other. It’s just about drawing as much of a line as possible between work and personal in this kind of situation.

That said, some1’s experience is crappy. The fact that the guy went around bragging about dating someone else in the office, but wanted to keep the relationship with some1 a secret is crappy and hurtful.

One relevant self-interview question: have I managed to stay friendly with most of my exes, or do my breakups mean that we never can see each other again? If the latter, consider that a breakup will probably mean you’d need to leave that workplace, so make your decision knowing that.

Great point, and a huge reason I don’t date people I work with. I am the sort of person who takes a few months of radio silence after a romance ends – no texts, calls, emails, I hide him on FB, etc., to reset the system. And with only one exception, I don’t resume contact. Not for any malicious reason; I don’t wish anyone ill. But once I’m over him it’s sort of like “Well, I’m doing fine not talking to you, so … do we really need to talk?” Dating someone I saw every day would make that no-contact rule impossible, and I know myself well enough to know that that’s not good for me.

I agree and I think another problem is that you also can’t know how the relationship will or won’t develop. There are multiple people I have dated casually and it’s not awkward at all to see them in a social or work-at-the-same-organization type context. But with someone I was in a serious relationship with that ended, we are just not part of each other’s lives anymore and working in the same place would be an impossible situation. And you can’t know ahead of time if it’ll be a casual NBD thing or something really important that changes the direction of your life.

Or even, to make it non-hypothetical, try to imagine your most recent ex taking a job at your company the day after your breakup. Then stretch it to the ex before that, and the ex before that, especially if the most recent was a particularly amicable breakup. I, personally, get a pit in my stomach when I see my most recent exes, and they were all amicable. My ex-husband, who I have a son with and have therefore been co-parenting with even since we “broke up,” I’m very detached from personally, at this point, but still would have NOT wanted to have around at my workplace immediately following.

Those thoughts keep me from even considering the idea of dating someone from the office (the fact that every single man in the office is already with someone, and I’m not really interested in dating at ALL right now both help, too!).

Another potential issue with dating a coworker that I don’t think anyone has mentioned is the “all your eggs in one basket” issue. It doesn’t become an issue until you are serious to the point of living together or getting married, but if the company has a downturn, you could both get laid off. Or the company has to try to keep at least one of you employed, which is preferrable to losing all your household income, but awkward for both partners in some way.

A relative and his spouse both work for a big company that has seen its share of layoffs. One was there first and the other came on board, which seemed kind of risky considering the company has struggled for a long time.

Yes, this is a very good thing to consider for engaged/married couples, especially before having kids or buying a house. This happened to a relative and it was devastating. After witnessing it, I vowed I would never put our family in that situation.

I dated a coworker and we stayed together after I got fired as a matter of fact she had heard through the grapevine that I was on thin ice and called me to let me know I was about to get canned. We got married and she continued to work there which was tough because I couldn’t go see her at work. Having said that I will end with this there is a reason there are sayings like pen and company ink and the like.

One of the best examples of how to do an office romance/breakup right comes from the set of The Big Bang Theory. Johnny Galecki and Kaley Cuocco had a long-term relationship and then broke up, and No One Knew It. Not even when their characters were romantically involved after the breakup did they discuss it. It only became public well after the fact.

Anon for Reasons touched on something else: the reputation of the person you date can affect your own. Especially if you’re new or don’t work in the same space, you may not realize you’re dating the office slacker/weirdo/gloomy gus/angry genius/incompetent jerk/inept jokester, etc. Worse (IME), if you’re wooed by someone with a history of lovin’ and leavin’, you’re the object of sympathy or scorn (when I was much younger and oh so naive). It’s not fair, but you can get labeled, and those labels DO affect your career. The reverse can happen too: If a mature, smart, capable person wants to date YOU, you look good too, as long as you’re not a loser–then the above warning applies to them.

Yeah, it may apply less to the OP who seems to know the lady fairly well, but if the object of your desire is going to (as Liz Phair so delicately put it) f— and run… that would be pretty humiliating in the office. So, you know, just be conscious of what you’re doing.

Which dovetails with… dating a coworker is murky and difficult to give a definitive up or down vote. However drunken hookups with coworkers are really a bad idea under like 99.9% of circumstances (the 30 year old voice of experience speaks to her 21 year old self)

I work at a small company (under 50 people) and met, married and had a child with a co-worker. We were VERY careful during the beginning of our relationship – not because we were worried about what our bosses would say. We wanted to keep the work environment as easy as possible for everyone else. That said – we work in different departments so some of the issues just wouldn’t exist. Like – I’m not in a position where I would have become his boss. Plus, our offices are on physically opposite sides of the building from each other. Wasn’t always easy but well worth it.

Let me add another warning for the awkwardness that comes when one of you is fired and the other still works there – especially in smaller companies where there are clearly no secrets.

Because it has been well over a year, and there are times I still have to step outside and take a breather because of some odd reminder that my husband is no longer sitting in the IT director’s office. It is tough.

Other considerations (only relevant if you intend this as a long-term relationship):

(1) What are the odds that one of you could become the other person’s boss? If it’s possible or likely, that can create serious relationship problems as well as serious job ethics problems.

(2) How will you feel if you date her, like her, get dumped by her, and then have to watch her enter into a relationship with a different co-worker? Would you be adult about that? Would she be adult if the reverse situation occurred? Some people can picture being civil to their ex – right up until they have to watch their ex engage in a relationship with another person every day at work, and work with that other person as well.

(3) If you are dating with the intent of eventually marrying, will marrying someone in your business make it harder for you both to find employment in the future? I work in a small field where it is incredibly difficult for two people to get a job in the same geographical area. If two people in my field marry each other, one person often has to give up on their career ambitions soon after marriage (or they end up living across the country from each other). Is that kind of thing a concern in your field?

I’ve been thinking about this and the cautious part of me says it’s a horrible idea, because the main part of my brain is always busy concocting worst case scenarios.

But it’s like any gamble – you could completely crap out and ruin your professional security at that job for someone it turns out you don’t even like…or you can find the love of your life and you guys make it work and a couple of bumps in the road at work are incidental.

Yeah – I’m kind of all or nothing in my thinking on this. I know there are a lot of degrees between lousy one night stand and grand passion.

In thinking about this I realized that I’ve seen a ton of these situations end badly, but I’ve also known people to meet at work and end up really happy. And if I were single where else would I meet anyone? My whole life is work, home, and occasional trips to the gas station and the store. So unless a guy worked one of those places, or showed up in my hallway at 2:00 am just to say hello – I wouldn’t meet him anyway.

I think the problem is that this is a question that may seem to be quite easy to answer in the abstract systems engineering sense (“potential complications, avoid”) which doesn’t take into account the fact that for a specifc individual the pay-off can be fantastic, and you don’t exactly choose who you are going to fall for by weighing pros and cons.

There are many academic disciplines where not only same-department couples are common, but they often collaborate together, and when they move universities they get poached as a pair. For these people, being able to work with your spouse is an important part of their relationship. Another example is husband and wife doctors working in the same practice.

As Jamie points out, some professions are just too involving and you are much more likely to meet somebody in the same line of work than a “civilian”, and often working with them is the easiest way to see them.

So yes, while it is very important to navigate workplace romances very carefully, because the pitfalls are real, you can’t just rule out every dating a co-worker, because it’s not like hiring an employee – you can’t just assume there’s an equivalent Mr/Mrs Right out there who is NOT a coworker that you should hold out for.

Basically: don’t sleep around the office, but if you think it might be “it”, the risk might very well be worth it.

It’s true about the acceptance of academia regarding professional couples (they actually talk about the “two-body problem” a lot, as an awful lot of academics have academic spouses; tenure-track jobs tend to be few and long-term; and many institutions are in areas without many outside job opportunities).

However, that only applies to married couples or domestic partnerships. Departmental dating can be just as fraught as in other workplaces, with the additional stress that comes from working in what may be a 30-year commitment in a small community.

(It says something, for example, that most of the single academic people I know either date less-ideal folks outside of campus or fret endlessly about the lack of local prospects, rather than date colleagues.)

“So yes, while it is very important to navigate workplace romances very carefully, because the pitfalls are real, you can’t just rule out every dating a co-worker, because it’s not like hiring an employee – you can’t just assume there’s an equivalent Mr/Mrs Right out there who is NOT a coworker that you should hold out for.”

Sure you can. I ruled out dating people in my entire field – including but not limited to co-workers.

I think if we’re honest about it, rather than idealistic, we’ll realize that lots of other people make exactly the same choice as I have. I’ve even had a small handful of co-workers tell me plainly that they would expect any woman they marry to follow them around as they advance in their career, without question – so I know I’m not the only one (though I’m the only woman that I know who feels this way, which perhaps makes me a freak). I made it clear to my current boyfriend that I put my career first, and he has accepted that for the time being. If he changes his mind, I will miss him terribly, but I will continue furthering my career.

This is a free country, and we can all go meet people outside of work. We aren’t locked into our places of business. I can rule out dating any arbitrary class of people I like, and my decision not to date co-workers at least has serious thought put into it. By contrast, one of my co-workers has a rule where he won’t date women with visible arm hair. I think ruling out people in my field is a better way to handle it than some other folks I’ve talked to who won’t date anyone who might make more money than they will – my choice is more about my personal employment and less about maintaining superiority in the relationship.

“Basically: don’t sleep around the office, but if you think it might be “it”, the risk might very well be worth it.”

I agree and disagree. You definitely shouldn’t be sleeping around the office because that gets around. But I don’t necessarily think you should only start something if you think the other person might be “it”. The serious relationships are usually the ones that end up blowing up and affecting your work. I’ve never had a casual relationship blow up, because there just wasn’t anything to blow up about. Don’t make it a habit, but if you work (not too closely) with someone and want to have a casual fling (and if both of you are mature enough) then I say go for it.

I am the child of an office romance that is now in it’s 32nd year of marriage. I am pretty pro-office romance; however I do agree that you should be smart, mature and discreet about it. In my parent’s case, they were friends before they got romantically involved so they knew each other pretty well–no big surprises about personality, work ethic, etc.

It’s also pretty difficult to meet someone and get to know them in a organic way after you are a “real grownup” so I personally wouldn’t tell anyone to close off that avenue.

Yes the stakes are higher but if it’s someone you could end up marrying and sharing your life with? Personally it’s a gamble I would find worth taking.

I totally forgot that my parents met when my dad was cutting code on punch cards and my mom was one of the hordes of teenage girls hired to feed the cards into the machine.

Since he was technically her boss, he was clearly not following best practices…but she worked there for three months and got a husband, four beautiful children, and a lovely home out of the deal. Which I think, as a young woman in the late 50’s, may have been the goal.

But Amanda brings up another really good point – for a lot of people it’s pretty hard to meet someone unless it is at work, given how much of grown-up life is lived there.

Amanda, I married someone I worked with and we have been married a little over 30 years now. It was never a problem. You get to know someone very well in a office. This office was a professional one and I knew he was good husband material. He had a promising future, good salary, we had fun together, were attracted to each other, mutual office friends. He treated me like a queen and showed me respect and love from the beginning. He and I were of the same religion, we were made for each other. We only dated 3 months and became engaged. He is the best thing that every happened to me.

I am amused at how many people are mentioning being married 30 years or so after dating a co-worker. It was more common back then I guess? I am another who met my husband on the job. We were co-workers in a bank and once it became known that we were dating he was put on a management training program so that we would not be working in the same department. (sexist much?) We have been happily married for 31 years.

LW, if you do go out on a date, make sure you talk about things other than work! I have had plenty of club/work friendships over the years that were great when we were sharing war stories or funny moments on the job, but tended to fizzle out after a while because we had practically nothing in common other than working for the same organization.

At my college job there were lots of romances. The ones in mature relationships NEVER gossiped about their partners. Teasing jokes is as serious as it got. Meanwhile, the immature ones would tell anyone who would listen all the problems. Also, the smartest way to go about it is to keep it a secret (“No we’re just good friends”) until they were serious. Yes, I’m advocating white lies. And then once they were serious, it was not a secret, but not a big deal (“yeah we’re dating now. Anyway what’s the schedule for today?). The goal is to make bystanders think you’re friends, and your coworkers to forget all together.

So this is not a comment on the pitfalls, but rather how to go about it if/when it does happen.

This is a very bad idea for someone in a “small office.” I worked in a large manufacturing plant but in the front office where there were only 20-ish employees. The short version of a very painful story is that I dated and married a co-worker who left me two days after I suffered a miscarriage. I had to talk to, request reports from, and otherwise act professionally until I was finally able to leave the job a year later.

If you were in a building with 1,000 employees and she was on another floor in a different department — I’d say okay. But in a small office — no. Bad, BAD idea!

No. I absolutely do not date people at work. It’s a total dealbreaker for me. I did it one time a long time ago, and never again.

If your SO and you have an argument at home, then you can go to work and forget about it for a while. But not if you see them at work, even if they’re not in the same department. There’s no escape from that, or a breakup either.

It’s bad enough if someone in your social circle dumps you. At least your not relying on them for your livelihood.

My mother and father worked together and when they got a divorce…let me tell you, it was terrible. My father was an abusive man. Now imagine having to go to work and meet him there. Eventually my mother found another job, but it was incredibly stressful.

Another side to this situation is to consider very carefully whether or not to get involved with one of your company’s clients. Did that when I was much younger, and still regret it as one of the stupidest things I’ve every done.

My boss says, “Don’t s&#! where you eat,” and if I weren’t married, I’d take that advice when dating. Not saying it can’t work for anyone — clearly, it does — but most relationships don’t work out in the end, and the potential downside of the very likely event of a breakup is pretty bad, even though the potential upside in the far less likely event of you being together forever is pretty great. I might feel differently if I didn’t live in a large city where I have plenty of ways to meet people outside of work, though.

And the smaller the company, the harder it is to make it work, of course!

A situation I saw recently between two family members which we didn’t know were related until this happened: Someone mentioned X was on sick leave. Someone joked innocently about X trying it on. Y jumps up and starts a row because as it turns out X is their sibling.

Also another issue from working with a family member: No matter how hard you try an arguement you are having outside the workplace will stay with you during the work day too. We always tried to drop it and leave it at the door but it still felt ‘odd’ and made both of us a little more stressed.

Are you willing to leave your job for the chance to date this coworker? If the answer is yes, then go ahead and ask her out. Whether this relationship ends up being true love or true hate, one person leaving the company may be a necessity at some point. The fact that your company is so small increases the chances of weird feelings/issues (for you, her and others), so, keep that in mind.

AAM’s points are great, as are many of the insights and examples in the comments. I really want to buy in because it all seems so logical, professional, and wise.

But, on the other hand, I think that love and relationships often involve a “throwing caution to the wind” type of approach. It’s hard to know which cautions should/would be thrown and which can’t/won’t. I think it’s even harder to gauge whether or not a specific romantic chance is worth taking and, yes, I think it usually feels like a chance, coworkers or not.

Ugh. Is there by any chance a 12-step program out there for those of us who really want to “just say no” to office romances but are afraid that we possibly wouldn’t?

The issue with dating a co-worker in this generations is that we tend to forget social media plays a part in the relationship as well and being in a predicament where you show case you inner world on line makes it easy to expose your relationships , so you could only Benefit in the beginning because it’s a breathe of fresh air with a woman/man you work with. But dealing with human beings we go through ups and downs more often then most that we need space form things that cause stress. And the last thing you need is stress on the job. It’s always a good idea took take chances when they have a higher percentage of an outcome but dating a co-worker shouldn’t be romantic it should be strictly professional. The cliche business never personal we tend to put ourselves in the worst situations because we ignore the conical thoughts that can actually help you. In my case I’ve tried it once and it didn’t work as planed later I got fired. And she started dating another co-worker. I know my situations is not everyone’s but because I realize that after trying that scenario in the work environment I would strongly advise never to try something that can end very bad.